Stadion: Court 1 Round: 25 Ground: Clay
| ITF - M25 - Den Haag | 2021/06/27 08:00 | Simon Freund v Lodewijk Weststrate | 1-6,3-6 |
| ITF - M25 - Alkmaar | 2021/06/23 09:00 | Simon Freund v Javier Barranco Cosano | 2-6,6-7 |
| ITF - M25 - Alkmaar | 2021/06/21 14:30 | Simon Freund v Tom Pisane | 6-0,6-1 |
| ITF - M25 - Alkmaar | 2021/06/20 13:30 | Simon Freund v Buvaysar Gadamauri | 6-2,7-5 |
| ITF - M15 - Helsinki | 2021/06/02 08:10 | Simon Freund v Sean Cuenin | 2-6,6-4,4-6 |
| ITF - M15 - Jerusalem | 2021/05/12 07:00 | Yshai Oliel v Simon Freund | 6-0,7-5 |
| ITF - M15 - Ramat Hasharon | 2021/05/06 07:00 | Simon Freund v Ben Patael | 5-7,1-6 |
| ITF - M15 - Ramat Hasharon | 2021/05/05 11:55 | Simon Freund v Christophe Clement | 6-4,6-0 |
| ITF - M15 - Bratislava | 2021/08/24 08:00 | Kristof Minarik v Obrad Markovski | 7-6,3-6,3-10 |
| ITF - M15 - Bratislava | 2021/08/23 09:00 | Samo Polakovic v Obrad Markovski | 5-7,3-6 |
| ITF - M15 - Bratislava | 2021/08/17 08:00 | Franco Roncadelli v Obrad Markovski | 7-6,6-1 |
| ITF - M15 - Bratislava | 2021/08/16 12:00 | Adria Soriano Barrera v Obrad Markovski | 2-6,6-3,8-10 |
| ITF - M15 - Novi Sad | 2021/08/01 11:15 | Simon Habsuda v Obrad Markovski | 1-6,6-3,11-9 |
| ITF - M15 - Sofia | 2021/07/04 06:30 | Obrad Markovski v Denislav Prodanov | 1-6,7-5,7-10 |
| ITF - M15 - Skopje | 2021/06/11 07:00 | Alexis Gautier v Obrad Markovski | 6-4,6-3 |
| ITF - M15 - Skopje | 2021/06/10 08:35 | Kalin Ivanovski v Obrad Markovski | 6-3,4-6,4-6 |